Cyclocondensation of thioamides and haloacetic acid derivatives provides only 4-thiazolidinones; Isomeric 5-thiazolidinones were not observed

Synthetic Communications

Volumn 44, Issue 2, 2014, Pages 231-236

  Kaminskyy, Danylo ^a   Gzella, Andrzej K ^b   Lesyk, Roman ^a  

^a DANYLO HALYTSKY LVIV NATIONAL MEDICAL UNIVERSITY   (Ukraine)

^b POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

Author keywords

4 thiazolidinones; 5 thiazolidinones; Cyclocondensation; X ray

Indexed keywords

4 THIAZOLIDINONE DERIVATIVE; ACETIC ACID DERIVATIVE; CYANO (4 OXO 3 PHENYLTHIAZOLIDIN 2 YLIDENE)ACETIC ACID ETHYL ESTER; CYANO [5 (4 METHOXYBENZYLIDENE) 4 OXO 3 PHENYLTHIAZOLIDIN 2 YLIDENE]ACETIC ACID ETHYL ESTER; ESTER DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; NUCLEOPHILE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOAMIDE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONCENTRATION RESPONSE; CYCLIZATION; CYCLOADDITION; CYCLOCONDENSATION; DRUG SYNTHESIS; INFLUENZA VIRUS A H5N1; ISOMER; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

EID: 84887413754     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2013.800551     Document Type: Article

References (20)

1. Lesyk, R. B.;, Zimenkovsky, B. S. 4-Thiazolidones: Centenarian history, current status, and perspectives for modern organic and medicinal chemistry. Curr. Org. Chem. 2004, 8, 1547-1577.
2. Jain, A. K.;, Vaidya, A.;, Ravichandran, V.;, Kashaw, S. K.;, Agrawal, R. K. Recent developments and biological activities of thiazolidinone derivatives: A review. Bioorg. Med. Chem. 2012, 20, 3378-3395.
3. Prabhakar, Y. S.;, Solomon, V. R.;, Gupta, M. K.;, Katti, S. B. QSAR studies on thiazolidines: A biologically privileged scaffold. Top. Heterocycl. Chem. 2006, 4, 161-249.
4. Tomasic, T.;, Masic, L. P. Rhodanine as a privileged scaffold in drug discovery. Curr. Med. Chem. 2009, 16, 1596-1629.
5. Lesyk, R. B.;, Zimenkovsky, B. S.;, Kaminskyy, D. V.;, Kryshchyshyn, A. P.;, Havryluk, D. Ya.;, Atamanyuk, D. V.;, Subtel'na, I. Yu.;, Khyluk, D. V. Thiazolidinone motif in anticancer drug discovery: Experience of DH LNMU medicinal chemistry scientific group. Biopolym. Cell. 2011, 27, 107-117.
6. Kaminskyy, D. V.;, Lesyk, R. B. Structure-anticancer activity relationships among 4-azolidinone-3-carboxylic acids derivatives. Biopolym. Cell. 2010, 26, 136-145.
7. Metwally, M. A.;, Keshk, E. M.;, Fekry, A.;, Etman, H. A. Synthesis of some new thiazolidin-5-one derivatives of pharmaceutical interest. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 2067-2079.
8. Metwally, M. A.;, Etman, H. A.;, Keshk, E. M.;, Fekry, A. Thiazolidin-5-ones: Synthesis and reactions. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 1039-1058.
9. El-Desoky, S. I.;, Bondock, S. B.;, Etman, H. A.;, Fadda, A. A.;, Metwally, M. A. Synthesis of some new thiazole derivatives of pharmaceutical interest. Sulfur Lett. 2003, 26, 127-135.
10. Kaminskyy, D.;, Khyluk, D.;, Vasylenko, O.;, Zaprutko, L.;, Lesyk, R. A facile synthesis and anticancer activity evaluation of spiro[thiazolidinone- isatin] conjugates. Sci. Pharm. 2011, 79, 763-777.
11. Bukowski, L. Some reactions of 2-cyanomethyl-3-3 H -imidazol[4,5- b ]pyridine with isothiocyanates: Antituberculotic activity of the obtained compounds. Pharmazie 2001, 56, 23-31.
12. Grabenko, A. D.;, Kulaeva, L. N.;, Pel'kis, P. S. Substituted arylamides of dithiocarboxylic acids, XIII: Synthesis of 2,3-disubstituted thiazolidin-4-ones. Chem. Heterocyc. Compd. 1970, 6, 1513-1514.
13. Fadda, A. A.;, Bondock, S.;, Rabie, R.;, Etman, H. A. Cyanoacetamide derivatives as synthons in heterocyclic synthesis. Turk. J. Chem. 2008, 32, 259-286.
14. Khalil, M.;, Berghot, M. A.;, Gouda, M. A. Synthesis and antibacterial activity of some new thiazole and thiophene derivatives. Eur. J. Med. Chem. 2009, 44, 4434-4440.
15. Metwally, M. A.;, Khalifa, M. E.;, Attia, E. A.;, Amer, F. A. New arylhydrazonothiazolidin-5-one disperse dyes for dyeing polyester fibers. Pol. J. Chem. Technol. 2010, 12, 1-6.
16. Dabholkar, V. V.;, Tripathi, D. R. Synthesis and antibacterial activity of isochromene and isoquinoline derivative. J. Heterocycl. Chem. 2011, 48, 529-532.
17. Mohareb, R. M.;, Sherif, S. M. Heterocyclic synthesis with isothiocyantes: Synthesis of several new polyfunctionally substituted thiophene, 4-thiazoline, and thiazolidinone derivatives. Arch. Pharm. 1991, 324, 469-471.
18. Hernandez, R. P.;, Rodriguez, J. D.;, De-Armas, H. N.;, Toscano, R. A. Ethyl cyano(4-oxo-3-phenyl-l,3-thiazolidin-2-ylidene)acetate. Acta Cryst. 1996, C52, 1731-1733.
19. Sidwell, R. W.;, Smee, D. F. In vitro and in vivo assay systems for study of influenza virus inhibitors. Antiviral. Res. 2000, 48, 1-16.
20. Ram, V. J.;, Haque, N.;, Singh, S. K.;, Nath, M.;, Shoeb, A. Polarized ketene dithioacetals, part II: Synthesis of S,S- And S,N-cyclic ketene to azoles and 1,3-dithiole-2-thiones. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 88, 155-161.